4, 4-di (chloromethyl)-2-pentanone



Patented Aug. 5, 1952 UNITED STATES PTENT OFFICE IA-DI (CHLOROMETHYL) -2-PENTAN ONE Kenneth E. Wilzbach, Chicago, Ill., assignor to United States Rubber Company, New York,

N. Y., a corporation of New Jersey No Drawing. Application December 14, 1948,

Serial No. 65,289

1 Claim. (Cl. 260-593) 1 2 This invention relates to a new chemical, denoted 4,4-di(ch1oromethy1)- -'9 1 Analygis Percent Percent Percent scribing to the formula Carbon Hydrogen Chlorine CHM 5 Found 45. so 6.73 38.88 CE3 C OH2 C CH3 Theory 45. 88 6- 6 38 70 Th 24d t h lhd The chemical can be prepared by reacting 2- f i a E5 5? y razone of the new com methyl-4,4-di(chloromethyl) -l pentene (dimer of methylallyl chloride) with an oxidizing agent, 10 Example 2 Oxygen, Ozone, permanganate salt? such as A solution of 25 g. of potassium permanganate potassium permanganate, the latter 96mg pref and 17 .g. of concentrated (96%) sulfuric acid erably employ in acid Solutlon- T world in 250 g. of water is gradually added in the ysis pr readily at and complete course of 24 hours to an agitated suspension of Within a feW hours. s 3 hours, Whereas the 15 8.5 g. of 2-methyl-4,4-di(chloromethyl) -1-penidation by permanganate is completed within 24 mm in 50 of Water at After the hours at about In both 0a$e5, the1'e are manganate solution has been decolorized the obtained high yields 2 414414011101? manganese dioxide formed is removed by filtramethyl) -2-pe t Wmch 15 Isolated p tion and the filtrate is extracted with diethyl ified by extraction and. subsequent fractional ether The extract is dried and fractionauy distillation. tilled to yield 6.0 g. of 4,4-di(chloromethyl)-2- This new compound is of particular utility as pentanona a synthetic inte e For example, upon Having thus described my invention, what I reaction with alkali it is readily converted claim and desire to protect by Letters Patent is: aCG YI- -m y m y y p p As a new compound, 4,4-di(chloromethyl)-.2-

The followin examples disclose my invention pentanona in more detail. KENNETH E. WILZBACH.

Example 1 REFERENCE C Seven grams of 2-methyl-4,4-di(chloro- S ITED methyD-l-pentene are dissolved in 100 ml. of The followmg references are of record m the commercial 90% formic acid and a stream of file of thls patent oxygen containing 6% of ozone is introduced into UNITED STATES PATENTS the solution at 0 C. at a rate of 140 mL/minute Number Name Date for a period of 3 hours. The solution is then di- 2,004,066 Whit-[more et a1 June 4 1935 luted with 50 g. of water, neutralized with aque- 2,338,393 Bauer et a1 Jan 1944 ous alkali, and extracted with diethyl ether. The extract is dried and fractionally distilled to OTHER REFERENCES yield about 6.5 g. of 4=,4-di(chloromethyl)-2- Wilzbach, Mayo and VanMeter: J. Am. Chem. pentanone, B. 74-75 C./3 mm; n 1.4705; sp. 40 Soc, vol. 70, pages 4069-4072 (1948). 

